Maslak, Veselin

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orcid::0000-0002-5735-3953
  • Maslak, Veselin (15)
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Author's Bibliography

Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study

Jakšić, Jovana; Milinković, Evgenija; Cvetanović, Katarina; Tokić-Vujošević, Zorana; Jovanov, Vladislav; Mitrović, Aleksandra; Maslak, Veselin

(Royal Society of Chemistry, 2024)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Milinković, Evgenija
AU  - Cvetanović, Katarina
AU  - Tokić-Vujošević, Zorana
AU  - Jovanov, Vladislav
AU  - Mitrović, Aleksandra
AU  - Maslak, Veselin
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5389
AB  - In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study
VL  - 26
IS  - 1
SP  - 517
EP  - 523
DO  - 10.1039/d3cp04322c
ER  - 
@article{
author = "Jakšić, Jovana and Milinković, Evgenija and Cvetanović, Katarina and Tokić-Vujošević, Zorana and Jovanov, Vladislav and Mitrović, Aleksandra and Maslak, Veselin",
year = "2024",
abstract = "In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study",
volume = "26",
number = "1",
pages = "517-523",
doi = "10.1039/d3cp04322c"
}
Jakšić, J., Milinković, E., Cvetanović, K., Tokić-Vujošević, Z., Jovanov, V., Mitrović, A.,& Maslak, V.. (2024). Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 26(1), 517-523.
https://doi.org/10.1039/d3cp04322c
Jakšić J, Milinković E, Cvetanović K, Tokić-Vujošević Z, Jovanov V, Mitrović A, Maslak V. Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics. 2024;26(1):517-523.
doi:10.1039/d3cp04322c .
Jakšić, Jovana, Milinković, Evgenija, Cvetanović, Katarina, Tokić-Vujošević, Zorana, Jovanov, Vladislav, Mitrović, Aleksandra, Maslak, Veselin, "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study" in Physical Chemistry Chemical Physics, 26, no. 1 (2024):517-523,
https://doi.org/10.1039/d3cp04322c . .

Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis

Jovanović, Miloš; Jovanović, Predrag; Tasić, Gordana; Simić, Milena; Maslak, Veselin; Rakić, Srđan; Rodić, Marko; Vlahović, Filip; Petković, Miloš; Savić, Vladimir

(John Wiley and Sons Inc, 2023)

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Maslak, Veselin
AU  - Rakić, Srđan
AU  - Rodić, Marko
AU  - Vlahović, Filip
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4953
AB  - Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.
PB  - John Wiley and Sons Inc
T2  - Advanced Synthesis and Catalysis
T1  - Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
DO  - 10.1002/adsc.202300301
ER  - 
@article{
author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir",
year = "2023",
abstract = "Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.",
publisher = "John Wiley and Sons Inc",
journal = "Advanced Synthesis and Catalysis",
title = "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis",
doi = "10.1002/adsc.202300301"
}
Jovanović, M., Jovanović, P., Tasić, G., Simić, M., Maslak, V., Rakić, S., Rodić, M., Vlahović, F., Petković, M.,& Savić, V.. (2023). Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis
John Wiley and Sons Inc..
https://doi.org/10.1002/adsc.202300301
Jovanović M, Jovanović P, Tasić G, Simić M, Maslak V, Rakić S, Rodić M, Vlahović F, Petković M, Savić V. Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis. 2023;.
doi:10.1002/adsc.202300301 .
Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena, Maslak, Veselin, Rakić, Srđan, Rodić, Marko, Vlahović, Filip, Petković, Miloš, Savić, Vladimir, "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis" in Advanced Synthesis and Catalysis (2023),
https://doi.org/10.1002/adsc.202300301 . .
2
2
1

Highly exo selective, photochemically promoted cyclization of iodoallene derivatives

Jovanović, Miloš; Simić, Milena; Petković, Miloš; Tasić, Gordana; Maslak, Veselin; Jovanović, Predrag; Savić, Vladimir

(Wiley Periodicals LLC, 2022)

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Tasić, Gordana
AU  - Maslak, Veselin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4175
AB  - A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1 mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.
PB  - Wiley Periodicals LLC
T2  - Journal of Heterocyclic Chemistry
T1  - Highly exo selective, photochemically promoted cyclization of iodoallene derivatives
VL  - 59
IS  - 8
SP  - 1435
EP  - 1440
DO  - 10.1002/jhet.4472
ER  - 
@article{
author = "Jovanović, Miloš and Simić, Milena and Petković, Miloš and Tasić, Gordana and Maslak, Veselin and Jovanović, Predrag and Savić, Vladimir",
year = "2022",
abstract = "A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1 mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.",
publisher = "Wiley Periodicals LLC",
journal = "Journal of Heterocyclic Chemistry",
title = "Highly exo selective, photochemically promoted cyclization of iodoallene derivatives",
volume = "59",
number = "8",
pages = "1435-1440",
doi = "10.1002/jhet.4472"
}
Jovanović, M., Simić, M., Petković, M., Tasić, G., Maslak, V., Jovanović, P.,& Savić, V.. (2022). Highly exo selective, photochemically promoted cyclization of iodoallene derivatives. in Journal of Heterocyclic Chemistry
Wiley Periodicals LLC., 59(8), 1435-1440.
https://doi.org/10.1002/jhet.4472
Jovanović M, Simić M, Petković M, Tasić G, Maslak V, Jovanović P, Savić V. Highly exo selective, photochemically promoted cyclization of iodoallene derivatives. in Journal of Heterocyclic Chemistry. 2022;59(8):1435-1440.
doi:10.1002/jhet.4472 .
Jovanović, Miloš, Simić, Milena, Petković, Miloš, Tasić, Gordana, Maslak, Veselin, Jovanović, Predrag, Savić, Vladimir, "Highly exo selective, photochemically promoted cyclization of iodoallene derivatives" in Journal of Heterocyclic Chemistry, 59, no. 8 (2022):1435-1440,
https://doi.org/10.1002/jhet.4472 . .

Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60

Jakšić, Jovana; Mitrović, Aleksandra; Tokić-Vujošević, Zorana; Milčić, Miloš; Maslak, Veselin

(Royal Society of Chemistry, 2021)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Mitrović, Aleksandra
AU  - Tokić-Vujošević, Zorana
AU  - Milčić, Miloš
AU  - Maslak, Veselin
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3982
AB  - In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
VL  - 11
IS  - 47
SP  - 29426
EP  - 29432
DO  - 10.1039/d1ra03944j
ER  - 
@article{
author = "Jakšić, Jovana and Mitrović, Aleksandra and Tokić-Vujošević, Zorana and Milčić, Miloš and Maslak, Veselin",
year = "2021",
abstract = "In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60",
volume = "11",
number = "47",
pages = "29426-29432",
doi = "10.1039/d1ra03944j"
}
Jakšić, J., Mitrović, A., Tokić-Vujošević, Z., Milčić, M.,& Maslak, V.. (2021). Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances
Royal Society of Chemistry., 11(47), 29426-29432.
https://doi.org/10.1039/d1ra03944j
Jakšić J, Mitrović A, Tokić-Vujošević Z, Milčić M, Maslak V. Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances. 2021;11(47):29426-29432.
doi:10.1039/d1ra03944j .
Jakšić, Jovana, Mitrović, Aleksandra, Tokić-Vujošević, Zorana, Milčić, Miloš, Maslak, Veselin, "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60" in RSC Advances, 11, no. 47 (2021):29426-29432,
https://doi.org/10.1039/d1ra03944j . .
2
2

Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials

Jakšić, Jovana; Ostojić, Sanja; Micić, Darko; Tokić-Vujošević, Zorana; Milovanović, Jelena; Karkalić, Radovan; O'Connor, Kevin E.; Kenny, Shane T.; Casey, William; Nikodinović-Runić, Jasmina; Maslak, Veselin

(John Wiley & Sons, Ltd., 2020)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Ostojić, Sanja
AU  - Micić, Darko
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, Jelena
AU  - Karkalić, Radovan
AU  - O'Connor, Kevin E.
AU  - Kenny, Shane T.
AU  - Casey, William
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3534
AB  - In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.
PB  - John Wiley & Sons, Ltd.
T2  - International Journal of Energy Research
T1  - Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials
VL  - 44
IS  - 2
SP  - 1294
EP  - 1302
DO  - 10.1002/er.4934
ER  - 
@article{
author = "Jakšić, Jovana and Ostojić, Sanja and Micić, Darko and Tokić-Vujošević, Zorana and Milovanović, Jelena and Karkalić, Radovan and O'Connor, Kevin E. and Kenny, Shane T. and Casey, William and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2020",
abstract = "In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.",
publisher = "John Wiley & Sons, Ltd.",
journal = "International Journal of Energy Research",
title = "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials",
volume = "44",
number = "2",
pages = "1294-1302",
doi = "10.1002/er.4934"
}
Jakšić, J., Ostojić, S., Micić, D., Tokić-Vujošević, Z., Milovanović, J., Karkalić, R., O'Connor, K. E., Kenny, S. T., Casey, W., Nikodinović-Runić, J.,& Maslak, V.. (2020). Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research
John Wiley & Sons, Ltd.., 44(2), 1294-1302.
https://doi.org/10.1002/er.4934
Jakšić J, Ostojić S, Micić D, Tokić-Vujošević Z, Milovanović J, Karkalić R, O'Connor KE, Kenny ST, Casey W, Nikodinović-Runić J, Maslak V. Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research. 2020;44(2):1294-1302.
doi:10.1002/er.4934 .
Jakšić, Jovana, Ostojić, Sanja, Micić, Darko, Tokić-Vujošević, Zorana, Milovanović, Jelena, Karkalić, Radovan, O'Connor, Kevin E., Kenny, Shane T., Casey, William, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials" in International Journal of Energy Research, 44, no. 2 (2020):1294-1302,
https://doi.org/10.1002/er.4934 . .
7
4
6

Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)

Lazić, Jelena; Spasić, Jelena; Francuski, Đorđe; Tokić-Vujošević, Zorana; Nikodinović-Runić, Jasmina; Maslak, Veselin; Đokić, Lidija

(Srpsko hemijsko društvo, Beograd, 2016)

TY  - JOUR
AU  - Lazić, Jelena
AU  - Spasić, Jelena
AU  - Francuski, Đorđe
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
AU  - Đokić, Lidija
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2690
AB  - Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)
VL  - 81
IS  - 8
SP  - 871
EP  - 881
DO  - 10.2298/JSC160222053L
ER  - 
@article{
author = "Lazić, Jelena and Spasić, Jelena and Francuski, Đorđe and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin and Đokić, Lidija",
year = "2016",
abstract = "Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)",
volume = "81",
number = "8",
pages = "871-881",
doi = "10.2298/JSC160222053L"
}
Lazić, J., Spasić, J., Francuski, Đ., Tokić-Vujošević, Z., Nikodinović-Runić, J., Maslak, V.,& Đokić, L.. (2016). Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 81(8), 871-881.
https://doi.org/10.2298/JSC160222053L
Lazić J, Spasić J, Francuski Đ, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V, Đokić L. Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society. 2016;81(8):871-881.
doi:10.2298/JSC160222053L .
Lazić, Jelena, Spasić, Jelena, Francuski, Đorđe, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, Đokić, Lidija, "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)" in Journal of the Serbian Chemical Society, 81, no. 8 (2016):871-881,
https://doi.org/10.2298/JSC160222053L . .
1
1
1

Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine

Tasić, Gordana; Maslak, Veselin; Husinec, Suren; Todorović, Nina; Savić, Vladimir

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - JOUR
AU  - Tasić, Gordana
AU  - Maslak, Veselin
AU  - Husinec, Suren
AU  - Todorović, Nina
AU  - Savić, Vladimir
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2375
AB  - The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
VL  - 56
IS  - 19
SP  - 2529
EP  - 2532
DO  - 10.1016/j.tetlet.2015.03.129
ER  - 
@article{
author = "Tasić, Gordana and Maslak, Veselin and Husinec, Suren and Todorović, Nina and Savić, Vladimir",
year = "2015",
abstract = "The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine",
volume = "56",
number = "19",
pages = "2529-2532",
doi = "10.1016/j.tetlet.2015.03.129"
}
Tasić, G., Maslak, V., Husinec, S., Todorović, N.,& Savić, V.. (2015). Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 56(19), 2529-2532.
https://doi.org/10.1016/j.tetlet.2015.03.129
Tasić G, Maslak V, Husinec S, Todorović N, Savić V. Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry. 2015;56(19):2529-2532.
doi:10.1016/j.tetlet.2015.03.129 .
Tasić, Gordana, Maslak, Veselin, Husinec, Suren, Todorović, Nina, Savić, Vladimir, "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine" in Tetrahedron-Asymmetry, 56, no. 19 (2015):2529-2532,
https://doi.org/10.1016/j.tetlet.2015.03.129 . .
4
4
4

Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain

Jovanović, Predrag; Jeremić, Sanja; Đokić, Lidija; Savić, Vladimir; Radivojević, Jelena; Maslak, Veselin; Ivković, Branka; Vasiljević, Branka; Nikodinović-Runić, Jasmina

(Elsevier Science Inc, New York, 2014)

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Savić, Vladimir
AU  - Radivojević, Jelena
AU  - Maslak, Veselin
AU  - Ivković, Branka
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2202
AB  - Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.
PB  - Elsevier Science Inc, New York
T2  - Enzyme and Microbial Technology
T1  - Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain
VL  - 60
SP  - 16
EP  - 23
DO  - 10.1016/j.enzmictec.2014.03.010
ER  - 
@article{
author = "Jovanović, Predrag and Jeremić, Sanja and Đokić, Lidija and Savić, Vladimir and Radivojević, Jelena and Maslak, Veselin and Ivković, Branka and Vasiljević, Branka and Nikodinović-Runić, Jasmina",
year = "2014",
abstract = "Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.",
publisher = "Elsevier Science Inc, New York",
journal = "Enzyme and Microbial Technology",
title = "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain",
volume = "60",
pages = "16-23",
doi = "10.1016/j.enzmictec.2014.03.010"
}
Jovanović, P., Jeremić, S., Đokić, L., Savić, V., Radivojević, J., Maslak, V., Ivković, B., Vasiljević, B.,& Nikodinović-Runić, J.. (2014). Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology
Elsevier Science Inc, New York., 60, 16-23.
https://doi.org/10.1016/j.enzmictec.2014.03.010
Jovanović P, Jeremić S, Đokić L, Savić V, Radivojević J, Maslak V, Ivković B, Vasiljević B, Nikodinović-Runić J. Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology. 2014;60:16-23.
doi:10.1016/j.enzmictec.2014.03.010 .
Jovanović, Predrag, Jeremić, Sanja, Đokić, Lidija, Savić, Vladimir, Radivojević, Jelena, Maslak, Veselin, Ivković, Branka, Vasiljević, Branka, Nikodinović-Runić, Jasmina, "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain" in Enzyme and Microbial Technology, 60 (2014):16-23,
https://doi.org/10.1016/j.enzmictec.2014.03.010 . .
5
5
5

Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst

Radivojević, Jelena; Minovska, Gordana; Senerović, Lidija; O'Connor, Kevin; Jovanović, Predrag; Savić, Vladimir; Tokić-Vujošević, Zorana; Nikodinović-Runić, Jasmina; Maslak, Veselin

(Royal Soc Chemistry, Cambridge, 2014)

TY  - JOUR
AU  - Radivojević, Jelena
AU  - Minovska, Gordana
AU  - Senerović, Lidija
AU  - O'Connor, Kevin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2107
AB  - Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.
PB  - Royal Soc Chemistry, Cambridge
T2  - Russian Journal of Genetics
T1  - Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
VL  - 4
IS  - 105
SP  - 60502
EP  - 60510
DO  - 10.1039/c4ra05517a
ER  - 
@article{
author = "Radivojević, Jelena and Minovska, Gordana and Senerović, Lidija and O'Connor, Kevin and Jovanović, Predrag and Savić, Vladimir and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2014",
abstract = "Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Russian Journal of Genetics",
title = "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst",
volume = "4",
number = "105",
pages = "60502-60510",
doi = "10.1039/c4ra05517a"
}
Radivojević, J., Minovska, G., Senerović, L., O'Connor, K., Jovanović, P., Savić, V., Tokić-Vujošević, Z., Nikodinović-Runić, J.,& Maslak, V.. (2014). Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics
Royal Soc Chemistry, Cambridge., 4(105), 60502-60510.
https://doi.org/10.1039/c4ra05517a
Radivojević J, Minovska G, Senerović L, O'Connor K, Jovanović P, Savić V, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V. Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics. 2014;4(105):60502-60510.
doi:10.1039/c4ra05517a .
Radivojević, Jelena, Minovska, Gordana, Senerović, Lidija, O'Connor, Kevin, Jovanović, Predrag, Savić, Vladimir, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst" in Russian Journal of Genetics, 4, no. 105 (2014):60502-60510,
https://doi.org/10.1039/c4ra05517a . .
3
3
2

Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B

Tasić, Gordana; Simić, Milena; Popović, Stanimir; Husinec, Suren; Maslak, Veselin; Savić, Vladimir

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - JOUR
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Popović, Stanimir
AU  - Husinec, Suren
AU  - Maslak, Veselin
AU  - Savić, Vladimir
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1973
AB  - Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B
VL  - 54
IS  - 34
SP  - 4536
EP  - 4539
DO  - 10.1016/j.tetlet.2013.06.069
ER  - 
@article{
author = "Tasić, Gordana and Simić, Milena and Popović, Stanimir and Husinec, Suren and Maslak, Veselin and Savić, Vladimir",
year = "2013",
abstract = "Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B",
volume = "54",
number = "34",
pages = "4536-4539",
doi = "10.1016/j.tetlet.2013.06.069"
}
Tasić, G., Simić, M., Popović, S., Husinec, S., Maslak, V.,& Savić, V.. (2013). Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 54(34), 4536-4539.
https://doi.org/10.1016/j.tetlet.2013.06.069
Tasić G, Simić M, Popović S, Husinec S, Maslak V, Savić V. Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry. 2013;54(34):4536-4539.
doi:10.1016/j.tetlet.2013.06.069 .
Tasić, Gordana, Simić, Milena, Popović, Stanimir, Husinec, Suren, Maslak, Veselin, Savić, Vladimir, "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B" in Tetrahedron-Asymmetry, 54, no. 34 (2013):4536-4539,
https://doi.org/10.1016/j.tetlet.2013.06.069 . .
9
6
8

Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase

Narancić, Tanja; Kadivojević, Jelena; Jovanović, Predrag; Francuski, Đorđe; Bigović, Miljan; Maslak, Veselin; Savić, Vladimir; Vasiljević, Branka; O'Connor, Kevin; Nikodinović-Runić, Jasmina

(Elsevier Sci Ltd, Oxford, 2013)

TY  - JOUR
AU  - Narancić, Tanja
AU  - Kadivojević, Jelena
AU  - Jovanović, Predrag
AU  - Francuski, Đorđe
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1960
AB  - A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
PB  - Elsevier Sci Ltd, Oxford
T2  - Bioresource Technology
T1  - Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
VL  - 142
SP  - 462
EP  - 468
DO  - 10.1016/j.biortech.2013.05.074
ER  - 
@article{
author = "Narancić, Tanja and Kadivojević, Jelena and Jovanović, Predrag and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin and Nikodinović-Runić, Jasmina",
year = "2013",
abstract = "A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Bioresource Technology",
title = "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase",
volume = "142",
pages = "462-468",
doi = "10.1016/j.biortech.2013.05.074"
}
Narancić, T., Kadivojević, J., Jovanović, P., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K.,& Nikodinović-Runić, J.. (2013). Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology
Elsevier Sci Ltd, Oxford., 142, 462-468.
https://doi.org/10.1016/j.biortech.2013.05.074
Narancić T, Kadivojević J, Jovanović P, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor K, Nikodinović-Runić J. Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology. 2013;142:462-468.
doi:10.1016/j.biortech.2013.05.074 .
Narancić, Tanja, Kadivojević, Jelena, Jovanović, Predrag, Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin, Nikodinović-Runić, Jasmina, "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase" in Bioresource Technology, 142 (2013):462-468,
https://doi.org/10.1016/j.biortech.2013.05.074 . .
22
17
18

A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations

Tasić, Gordana; Ranđelović, Jelena; Vusurović, Nikola; Maslak, Veselin; Husinec, Suren; Savić, Vladimir

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - JOUR
AU  - Tasić, Gordana
AU  - Ranđelović, Jelena
AU  - Vusurović, Nikola
AU  - Maslak, Veselin
AU  - Husinec, Suren
AU  - Savić, Vladimir
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1924
AB  - Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations
VL  - 54
IS  - 18
SP  - 2243
EP  - 2246
DO  - 10.1016/j.tetlet.2013.02.068
ER  - 
@article{
author = "Tasić, Gordana and Ranđelović, Jelena and Vusurović, Nikola and Maslak, Veselin and Husinec, Suren and Savić, Vladimir",
year = "2013",
abstract = "Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations",
volume = "54",
number = "18",
pages = "2243-2246",
doi = "10.1016/j.tetlet.2013.02.068"
}
Tasić, G., Ranđelović, J., Vusurović, N., Maslak, V., Husinec, S.,& Savić, V.. (2013). A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 54(18), 2243-2246.
https://doi.org/10.1016/j.tetlet.2013.02.068
Tasić G, Ranđelović J, Vusurović N, Maslak V, Husinec S, Savić V. A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron-Asymmetry. 2013;54(18):2243-2246.
doi:10.1016/j.tetlet.2013.02.068 .
Tasić, Gordana, Ranđelović, Jelena, Vusurović, Nikola, Maslak, Veselin, Husinec, Suren, Savić, Vladimir, "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations" in Tetrahedron-Asymmetry, 54, no. 18 (2013):2243-2246,
https://doi.org/10.1016/j.tetlet.2013.02.068 . .
4
4
4

A Useful Synthetic Equivalent of a Hydroxyacetone Enolate

Bigović, Miljan; Maslak, Veselin; Tokić-Vujošević, Zorana; Divjaković, Vladimir; Saičić, Radomir N.

(Amer Chemical Soc, Washington, 2011)

TY  - JOUR
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Divjaković, Vladimir
AU  - Saičić, Radomir N.
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1482
AB  - Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - A Useful Synthetic Equivalent of a Hydroxyacetone Enolate
VL  - 13
IS  - 17
SP  - 4720
EP  - 4723
DO  - 10.1021/ol2019357
ER  - 
@article{
author = "Bigović, Miljan and Maslak, Veselin and Tokić-Vujošević, Zorana and Divjaković, Vladimir and Saičić, Radomir N.",
year = "2011",
abstract = "Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate",
volume = "13",
number = "17",
pages = "4720-4723",
doi = "10.1021/ol2019357"
}
Bigović, M., Maslak, V., Tokić-Vujošević, Z., Divjaković, V.,& Saičić, R. N.. (2011). A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters
Amer Chemical Soc, Washington., 13(17), 4720-4723.
https://doi.org/10.1021/ol2019357
Bigović M, Maslak V, Tokić-Vujošević Z, Divjaković V, Saičić RN. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters. 2011;13(17):4720-4723.
doi:10.1021/ol2019357 .
Bigović, Miljan, Maslak, Veselin, Tokić-Vujošević, Zorana, Divjaković, Vladimir, Saičić, Radomir N., "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate" in Organic Letters, 13, no. 17 (2011):4720-4723,
https://doi.org/10.1021/ol2019357 . .
8
5
6

Palladium-catalyzed cross-couplings of allylic phosphates

Maslak, Veselin; Tokić-Vujošević, Zorana; Saičić, Radomir N.

(Pergamon-Elsevier Science Ltd, Oxford, 2009)

TY  - JOUR
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Saičić, Radomir N.
PY  - 2009
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1220
AB  - A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Palladium-catalyzed cross-couplings of allylic phosphates
VL  - 50
IS  - 16
SP  - 1858
EP  - 1860
DO  - 10.1016/j.tetlet.2009.02.026
ER  - 
@article{
author = "Maslak, Veselin and Tokić-Vujošević, Zorana and Saičić, Radomir N.",
year = "2009",
abstract = "A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Palladium-catalyzed cross-couplings of allylic phosphates",
volume = "50",
number = "16",
pages = "1858-1860",
doi = "10.1016/j.tetlet.2009.02.026"
}
Maslak, V., Tokić-Vujošević, Z.,& Saičić, R. N.. (2009). Palladium-catalyzed cross-couplings of allylic phosphates. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 50(16), 1858-1860.
https://doi.org/10.1016/j.tetlet.2009.02.026
Maslak V, Tokić-Vujošević Z, Saičić RN. Palladium-catalyzed cross-couplings of allylic phosphates. in Tetrahedron-Asymmetry. 2009;50(16):1858-1860.
doi:10.1016/j.tetlet.2009.02.026 .
Maslak, Veselin, Tokić-Vujošević, Zorana, Saičić, Radomir N., "Palladium-catalyzed cross-couplings of allylic phosphates" in Tetrahedron-Asymmetry, 50, no. 16 (2009):1858-1860,
https://doi.org/10.1016/j.tetlet.2009.02.026 . .
22
25
26

A useful synthetic equivalent of an acetone enolate

Maslak, Veselin; Tokić-Vujošević, Zorana; Ferjancić, Zorana; Saičić, Radomir N.

(Pergamon-Elsevier Science Ltd, Oxford, 2009)

TY  - JOUR
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Ferjancić, Zorana
AU  - Saičić, Radomir N.
PY  - 2009
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1204
AB  - 2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - A useful synthetic equivalent of an acetone enolate
VL  - 50
IS  - 48
SP  - 6709
EP  - 6711
DO  - 10.1016/j.tetlet.2009.09.113
ER  - 
@article{
author = "Maslak, Veselin and Tokić-Vujošević, Zorana and Ferjancić, Zorana and Saičić, Radomir N.",
year = "2009",
abstract = "2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "A useful synthetic equivalent of an acetone enolate",
volume = "50",
number = "48",
pages = "6709-6711",
doi = "10.1016/j.tetlet.2009.09.113"
}
Maslak, V., Tokić-Vujošević, Z., Ferjancić, Z.,& Saičić, R. N.. (2009). A useful synthetic equivalent of an acetone enolate. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 50(48), 6709-6711.
https://doi.org/10.1016/j.tetlet.2009.09.113
Maslak V, Tokić-Vujošević Z, Ferjancić Z, Saičić RN. A useful synthetic equivalent of an acetone enolate. in Tetrahedron-Asymmetry. 2009;50(48):6709-6711.
doi:10.1016/j.tetlet.2009.09.113 .
Maslak, Veselin, Tokić-Vujošević, Zorana, Ferjancić, Zorana, Saičić, Radomir N., "A useful synthetic equivalent of an acetone enolate" in Tetrahedron-Asymmetry, 50, no. 48 (2009):6709-6711,
https://doi.org/10.1016/j.tetlet.2009.09.113 . .
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9